GB881265A - Quaternary ammonium compounds and their preparation - Google Patents

Abstract

The invention comprises quaternary ammonium compounds containing a cation of the formula <FORM:0881265/IV (b)/1> wherein X is a halogen atom or a methyl or a nitro group, R1 is an ethyl, 2-hydroxyethyl, isopropyl or allyl group when NR2R3 is a dimethyl or pyrrolidino group, or R1 is a methyl group when R2 and R3 are the same or different and are ethyl or 2-hydroxyethyl groups, and the preparation thereof by quaternisation of a tertiary amine having all but one of the groups desired in the quaternary ammonium compound attached directly to the nitrogen atom, with a reactive derivative RZ, wherein R is the group it is desired to introduce and Z is a reactive atom or group. Compounds wherein NR2R3 is a pyrrolidino group are also prepared by intra molecular condensation of a tertiary amine of the general formula <FORM:0881265/IV (b)/2> or reacting an appropriate secondary butylamine with a 1,4-disubstituted butane, Z-(CH2)4-Z. 1 - Hydroxy - 2-o-methylbenzylaminoethane is prepared from o-methylbenzylamine and ethylene oxide. N - o - Chlorobenzyl - N - isopropylamine is prepared from o-chlorobenzyl chloride and isopropylamine. Similarly are prepared, N-o-bromobenzyl - N,N - dimethylamine, - N - isopropylamine, - pyrrolidine, - N - ethylamine, N - o - chloro-benzylpyrrolidine N - o - methylpyrrolidine and N-o-fluorobenzyl-N,N-dimethylamine. o-Bromobenzyl alcohol esterified with p-toulene-sulphonyl chloride gives o-bromobenzyl p-toluene-sulphonate. o-Bromobenzyl bromide is reacted with ethyl 4-hydroxybutylamine to yield N-o-bromobenzyl-N-ethyl-N-4-hydroxybutylamine in turn reacted with hydriodic acid to give N-o-bromobenzyl-N-ethyl-N-4-iodo butylamine hydriodide. Specification 765,850 is referred to.ALSO:Pharmaceutical preparations comprise quaternary ammonium compounds containing a cation of the general formula <FORM:0881265/VI/1> wherein X is a halogen atom or a methyl group or a nitro group, R1 is an ethyl, 2-hydroxyethyl, isopropyl or allyl group when NR2R3 is a dimethylamino or pyrrolidino group or R1 is a methyl group when R2 and R3 are the same or different and are ethyl or 2-hydroxyethyl groups together with a suitable carrier therefore. The compositions may be in the form of tablets, powders, granules, capsules, cachets, suspensions or solutions for oral administration, solutions and suspensions for parenteral administration or suppositories and pessaries. Specification 765,850 is referred to.